Picking the Right Game > Being the Best Player

On finding the right career path

Jack Raines
August 16, 2021

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Two Paths - Human Eyes

Back in high school, I loved both football and basketball. It may surprise you that even though I played college football for five years, I actually enjoyed basketball more. Football is militaristic by nature. A typical game is composed of ~120 scripted, short bursts of energy. 90% of the game is executing your role on each snap, and 10% is making plays within that role. On a typical third down, I would have to hit my specific gap at a specific time to fit our broader defensive scheme. It was still on me to “beat” my guy, but I had to win my battles within the parameters of the play call.

Basketball is the opposite. 10% of basketball is executing set plays, and 90% is creating your own scoring opportunities. We were free to screen, cut, and shoot based on the flow of the game. I loved this inherent freedom behind basketball. Skilled football players execute. Skilled basketball players create.

Marc Antony once said, “Do what you love, and you’ll never work a day in your life.” My two cents: that quote is bullshit.

There is no doubt that I loved basketball more than football, but God built me to play football, not basketball. At 6’3 and 225 pounds, I had the frame and dimensions to play tight end or defensive end at a high level in college. Those same dimensions put me at a serious disadvantage as a basketball power forward. The average college big man is at least 6’8. In high school, I overcame the height issue by out-muscling opponents, but that would never work at the next level.

I was better at football. I was a four year starter on both sides of the ball, and I received letters from college coaches every week. I only started my senior year on the basketball team, and I was anything but a natural talent (though I did make All-Region honorable mention 😤). Realistically, my basketball career would have peaked at the Division Three level. Meanwhile, I had multiple opportunities to play Division One football. I may have enjoyed basketball a bit more than football, but I knew that football would take me farther than basketball ever could. It was a no brainer, and I went on to enjoy a fulfilling football career.

Cool Story Bro, Why Should I Care?

I chose football because it was a game that 1) I enjoyed and 2) I could succeed in. However, this idea of choosing the right game is infinitely more important in our careers than it ever was for my college athletics experience. Ironically, we spend 1% of our time choosing our career arc, and 99% of our time grinding away on said path. Not being intentional with our career choices poses two risks:

1) You invest too much time in an area where you probably won’t succeed.

2) You coast through your professional life on autopilot, never considering what you actually want to do.

One glance at a college roster showed me that my basketball upside would be limited after high school. This same dynamic is at play in the professional world. Take investment banking as an example. This is a notoriously competitive field. Most banks only take applicants from top schools (Harvard, Stanford, Yale, Princeton, etc.) and only a fraction of new analysts stick around long enough to move up the food chain. If you’re not an exceptional candidate willing to grind out 80 hour weeks, you’re going to struggle to succeed here.

On the flip side, you could take the first job that you get, and toil away mindlessly without considering alternatives. The path of least resistance is staying on your current course, and it is dangerously easy to spend years working on autopilot. You might wake up a decade later and realize you spent 10 years on something you never cared all that much about.

Maybe you’re stuck in one of these two cycles right now. You want to make a change, but you have no idea how. Questioning your career arc is pretty nerve wracking. First you have to admit that you are wrong, and you aren’t doing the thing that you should be doing. Second, you have to decide what you should be doing. There’s a million career paths out there. How are you supposed to figure out where to go?

You’re in luck. As someone who has been struggling with this myself, I made a nine point list to figure out what I should do next. This list has a 100% success rate (sample size: 1, me), so you know it’s trustworthy.

Answer the following nine questions:

  • How do I want to spend my time?
  • How can I get paid to do this?
  • Can I afford my lifestyle with this career path?
  • Am I good at this (or can I realistically get good)?
  • Is this something that I enjoy (or at least pleasantly tolerate?)
  • How competitive is this field?
  • How much room do I have to grow?
  • Can this opportunity yield other opportunities, or will I get stuck?
  • Do I know anyone who already succeeded here; can they mentor me?

If you can be honest with yourself here, you’ll be able to build the career that you desire. You don’t have to be the best of the best. You just need a career that leverages your strengths and interests while minimizing competition to help you succeed.

Something else to keep in mind, and I’ll probably write on this in detail later, is that the total market for opportunities is way bigger than most people realize. Nick Huber has built a multi-million dollar self-storage business, and he put together a list of overlooked businesses that can make you a ton of money. All sorts of “unsexy” businesses like pressure washing, carpet cleaning, and pet grooming can provide six-figure incomes to interested parties. On top of that, the creator economy has never been stronger. Youtube, TikTok, Instagram, Shopify, Substack, Facebook, Twitter, and countless other sites have removed all barriers to entry for online content and businesses. Don’t be afraid to look at “nontraditional” career paths. You might just find the perfect niche.

So What Is My Game?

I want to be a writer. Ironic for a finance major, I know.

A year or so into my career, I realized that the 9-5 wasn’t for me. I wanted to work on my own terms. How could I make enough money doing something I enjoyed to accomplish this goal?

I traded stocks a lot last year, and I made some great returns. I knew that I didn’t want to spend the next decade staring at charts, but I put my newfound knowledge to work by writing paid investment articles for Seeking Alpha. Then I leaned into the opposite side of scale and wrote satire for Hard Money. Along the way, dozens of people reached out to me asking about investments and personal finance. One day, it all clicked. I could start my own newsletter discussing personal finance, careers, and everything else that 20-somethings would want to read. I would write the information that I wish I had read a year ago.

Writing in public provides a few benefits:

  • It builds an audience
  • It provides opportunities to connect with others
  • It gives me a portfolio of published work

Naturally, I wanted to know if this could eventually become a profitable endeavor OR lead to another opportunity. It turns out that writing can do both. I follow a few writers who make $500k+ each from online newsletters, and their work is awesome. Companies will pay a ton to advertise on decent sized publications. Sharing my work online has also led to interesting conversations with people from all over the place. I’m currently talking to a few different parties about doing paid work for them.

Back to those nine points I listed earlier. How does my plan fit this framework?

So far, so good.

Closing Remarks

Spend more time finding the right game, and less time grinding away aimlessly. Once you find the career path that best leverages your attributes, you just have to stay in the game long enough to let it develop. Taking the time to solve your own career puzzle is frustrating and uncomfortable, but it is one of the most important decisions that you can make.

Have a great week,

Jack

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