What Career Is Right for Me

What Career Is Right for Me?: 10 Lessons on Finding Your Path

No one wants to be in a job they hate. For various reasons, many of us find ourselves in that situation. Whether you’re just out of college looking for your first job or several years into a position you despise, “What career is right for me?” is a question in need of an answer.

In this post, we’ll explore ten lessons that will help you answer the question, “What career is right for me?”

I’ll start by sharing my story. There are many lessons you may find helpful in it.

My Journey

When I was growing up, I lived in blissful ignorance of the real world. My dad was (and is) an entrepreneur, so I thought I would become a businessman much of the time.

With that said, I also whipsawed between any of several possible vocations. At one point, I wanted to be an orthopedic surgeon. Oddly specific, I know, until you consider that I liked the doctor who cared for my broken thumb.

Later on, I was sure I wanted to be in the army. At that point in my life, I was convinced that being “just a civilian” was some kind of second-class citizenship.

Finally, in college, I took a course on Financial Theory, which occurred right around the time I had to get serious about interviewing for internships that would set the course for future employment. That was when the Wheel of Fortune spinner stopped spinning.

The result? The thought that – “Hey, this hedging thing seems pretty fascinating, and it sounds like finance pays pretty well” led to an 8-year stint on Wall Street trading derivatives.

Why Do We Do This to Ourselves?

I was very fortunate not to be resource-constrained or short on free time during college. And yet the way I picked my career was so random.

I lucked out. My mental game of Career Musical Chairs was one in which the music stopped while I was practically already sitting in a spot that was particularly well-suited to my temperament and goals. That was pretty good of all the places to spend the first eight years after college.

That is, it was a great job. But it wasn’t the right career.

I should have taken it upon myself to research the potential careers I might enter. Instead, I sat in my dorm room and played Starcraft II.

If you’re lucky, you get to participate in some form of Take Your Son/Daughter to Work Day as a kid. But even if you have two parents who work outside the home in different industries, that still gives you practically zero education on what it is like to live life day in and day out in those lines of work.

Try Before You Buy

Sure, you may be able to land an internship at your eventual employer before you begin full-time. If you’re lucky, it may even be a rotational internship that lets you sample a few different roles at the firm. But by and large, people enter the workforce with virtually no knowledge of the career alternatives available to them.

It’s no wonder that the younger generation is switching jobs with such frequency and vigor – the odds of stumbling into your ideal career on your first try are practically nil.

In my own life, I had come to assume that work was nothing more than selling time for money, and fulfillment would have to wait. I was convinced that the whole “meaningful work” thing was just a Millennial Pipe Dream, a luxury I could only afford once I was done making money.

In reaction to this line of thought, I became a Mr. Money Mustache acolyte and tried to sprint to the finish line. I saved money on hand soap by using the restroom before I left the office instead of right when I got home. I lived in Manhattan, arguably the food capital of the world, and my favorite date spot with my wife was the Outback Steakhouse on 23rd Street.

It wasn’t until seven years into my career that I discovered that there even existed a form of work that could theoretically pay the bills, while actually being intrinsically satisfying for me. That turned the sprint mentality on its head.

To Be Fair

While that first job wasn’t my always-and-forever (and I knew that going in), I am tremendously grateful for it. As I mentioned in my recent post called “I Hate My Job,” if we keep going to work, we’re admitting we don’t hate our jobs, all things considered.

Frankly, if it weren’t for that first job, I wouldn’t have my current job (building ChroniFI). My time trading derivatives taught me a ton about how to live and how to think about risk. It also put me in the financial position to be able to overcome my personal risk aversion and try my hand at entrepreneurship.

Was that first job at a big bank fun? Sometimes, but generally no. But it gave me what I needed at that stage of my life. Sometimes that’s enough.

Lesson #1: If you don’t like your job, make sure it is at least putting you in a position to get a job you want later on.

Following Your Dreams and Other Errors

So it’s clear that “following your dreams” immediately upon graduation is not necessarily the right call. Unless money is no object. In that case, you do you. And congratulations.

For the rest of us, chances are it is our responsibility to think about money when making our career choices. There’s a ditch on both sides of the road, though. You can think too little about money and wind up hat in hand looking for handouts. Or you can focus too much on money and wind up a rich old miser who never knew what money was even good for.

Lesson #2: Know when it is time to stop working for money and start working for fulfillment.

Those of us familiar with the FIRE movement are quick to point out that there is a middle road – pursuing Financial Independence. In many cases, this entails making a lot of money early so money is no object later.

For me, that plan just didn’t fit. I’m one of those people who is cursed with the affliction of not being satisfied with a life that consists of only leisure. A week and a half into a vacation from a job I didn’t love somehow left me itching to get back to work…

Lesson #3: It is more important to know what you are retiring TO than what you are retiring FROM.


I’m also one of those people who was born without the gene for moderation. Somehow having only one cookie, or playing only one game of Agricola, only triggers a desire for five more.

Same goes for my career – my plan was to sprint to the finish line of Financial Independence and then take an epic victory lap. Most people would think this refers to a trip around the world or a fancy house and a Tesla in the driveway. For me, it would be a months-long board-game-a-palooza. What can I say? I’m cheap to please.

My thinking was “Financial Independence ASAP, and happiness eventually.” It took me a long time to find out that I had it exactly backward.

Lesson #4: Pursue happiness ASAP, and Financial Independence eventually, not the other way around.

Life Goals

As I wrote in my article on “Life Goals,” stepping back to examine your ultimate why is an important part of planning your life. But we need to live balanced lives that respect our weaknesses as humans.

For me, the superordinate goal is the well-being of my children. Around the time my then-2-year-old told me her favorite thing was to walk on grass, I realized I needed to choose a career that would enable me to give her some grass on which to walk.

What I’m talking about here is alignment. Sometimes we get so distracted by the how of what we’re doing that we neglect to consider the why. In my head, giving my kids a good life was translated into the heuristic of making money to support that life. But what happens when your pursuit of money impedes the purpose of the money itself?

Lesson #5: Don’t let the how obscure the why.

How To Find the Right Career

The way I found the right career for me was pretty simple. Living my life, and making room for trying new things. Early in my career, I was hell-bent on optimizing every hour of my life. I knew what I wanted (or so I thought), and I worked hard to ensure there was no slack in my life. Each minute that was not allocated toward an activity with a known payoff was a crime against my day.

What I was missing at that point was an appreciation of the fact that growth comes from stepping into the unknown. I was chronically under-allocating my time to the category of “New Pursuits.”

Thankfully, a lateral hire we made late in my career (and now a great personal friend) woke me up. He suggested I try learning to code. I did. And I loved it.

Lesson #6: Create slack in your life and be intentional about trying new things.

Creating Space

I’ve now learned that one of the best ways to pick the right path is by giving yourself options. That is, cultivate skills in unfamiliar domains. Meet new people and build new relationships. Experiment with new sports or hobbies.

Whatever it is, explore.

For my children, I dream of attempting to engineer a program for them and their friends to participate in a “Take Your Friend’s Son/Daughter to Work Day.” And then do it over and over until they’ve seen what it might be like to be a lawyer, a fireman, a physicist, or a baker. No, one day is not enough to know what any vocation is like, but it may give you an inkling of which ones deserve further research.

I was lucky to stumble into a first job that was a great solution for that period of my life. But I don’t want my kids to depend on luck. I want to give them the visibility to attenuate luck’s effect on this aspect of their lives.

For those of you who are already in a job, take a step back and ask yourself what you really want out of life. If your current job is a stepping-stone along that path, then appreciate it and enjoy the ride. Don’t forget to move on to the next stone when the time comes.

If your current job is not such a stepping-stone, move on.

Lesson #7: If your current job is a stepping-stone along the path toward your ideal life, then appreciate it as such.


It is much easier said than done when you reach a point where it’s time to move on (either to the next stone or to a different path altogether). But you can stack the deck in your favor.

Analyze your situation and see when you can afford to switch jobs (there’s an app for that 😉). Once you’ve simplified your situation, drink deep of the wisdom of others. Read books like “Your Money or Your Life” by Vicki Robin and Joe Dominguez and “The Simple Path to Wealth” by JL Collins.

And don’t be ashamed to just dive into some good-old-fashioned fitness quotes to help you power through the tough spots.

Lesson #8: Motivation is every bit as important as knowing the right action to take.

The Truth

The career that is right for you is the one that enables you to live your best life. Sounds meaningless, right? It’s not.

I spent 8 years at a job that made me constantly wait for the 60 hours of freedom between Friday evening and Monday morning. But I’m confident that that period was a part of me living my best life. It set me up to be able to have a job now that makes Monday mornings one of the most exciting times of the week.

If you feel that way about your job and it pays the bills in a long-term sense, you have already won.


So here are the steps toward finding your ideal career:

  1. Ask yourself if you know of a realistic career that will make your financial life work out long term and make you excited to go to work. If yes, do that – you win. If no, proceed to step 2.
  2. Create space in your life to explore new things. Purposefully allocate time to learning about all the different ways you could spend your time. Additionally, force yourself to meet new people. Leverage their experiences to expand your understanding of the world.
  3. Diligently save money. Over time, your savings will grow to a point that careers that had insufficient pay to sustain your desired lifestyle are no longer insufficient – you can complement that income with your investment returns. Your solution set has expanded with your newfound knowledge (hobbies, skills, and relationships) and bigger bank account. With this expansion in mind, return to step one.

Lesson #9: Leave yourself in a better position tomorrow than you were today.

It may not happen overnight, but you will move closer to the right career with each rotation through this cycler. The number of ways to make money that are visible to you will grow with your experience, and your strengthening finances will put a larger share of these options within your reach.

Lesson #10: Enjoy your life along the way.

While you follow this process, don’t be afraid to take a shallower path to Financial Independence if it eventually gets you where you need to be and allows you to enjoy your life. The present is all you have, so get out there and make it count.

This article was produced and syndicated by Wealth of Geeks.

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