Were You Happier Before the Law?

In 2020, I made over $300,000 from a full-time job and a side business.

I was disappointed and upset that it was probably going to be around $250,000 in 2021 after switching jobs. I ended up making around $280,000, so I wasn’t that upset anymore.

In 2023, I expect to make around $450,000. I don’t feel any different even though it’s a larger amount than before.

The more you make, the higher your personal record, the higher the threshold becomes for feeling like a human being.

I want more and more in order to feel like I have a future. Maybe it’s the inflation. Maybe it’s an addiction.

Admit it: One of the reasons—if not the main reason—for staying in law is the money.

There are sacrifices associated with that. Social life. Dating life. Relationships. Friends and family. Your sense of humor. Your personality. Your soul.

They say money is the root of all evil. Someone will inevitably chime in to say it’s the love of money that’s the root of all evil.

But I hate money. You don’t get addicted to what you love.

Honestly, I was happiest when I was making under $38,000 before law school, an innocent soul who was free.

I had my own studio, little responsibility, and all the time to myself outside of work time. Sure, I had to chase down roaches in my flat, but imagine that being the biggest worry you have. I had it good. I was young. I didn’t have to count calories. I had no worries. I played video games and talked to my crush.

Now I’ve built a career and a business that I’m beholden to. I have customers to answer to. I have responsibilities at work. I have times when I despise my job. My business with its creative freedom is the one thing that keeps me sane. All my time is spent in both places, making all this money without the will to spend it on anything.

Despite making above-average income, I don’t (can’t) even spend my money like a normal person.

The top spending category in America is rent. Mine is index funds and options trades that go sour. My self-worth is correlated to my brokerage account.

The more I make, the more it becomes my identity. I have to keep surpassing the high score.

Most people won’t understand this. They’ll call you privileged for working hard and making sacrifices to get to where you are, only to be trapped in the golden handcuffs. Feels more like a double-edged sword than a privilege.

I can’t even share these numbers with anyone lest they resent or expect things from me. My sister already weaponized my income (a downplayed amount) against me.

If I have “career privilege,” they have “happiness privilege.”

The most fortunate people are those who are happy to make a modest living but have a normal life, with friends and relationship(s).

One of my ex-girlfriends had friends who were just scraping by, but they’d always seem happy working on things they enjoyed and hanging out eating good food with friends.

I get jealous of them when I watch their Instagram stories.

I get jealous of people who spend freely and post about it online. Nice trips, meals, toys. It means they are OK with working much longer than I plan to because they enjoy their career. Or maybe they are sponsored by a spouse or other people. Or they’re not seeing the consequences that I see (which makes me feel like a crazy person).

I will be able to reach financial freedom much earlier than them, but they’ll always have social support. I envy them because it seems more fulfilling than finding “freedom.” They already have it.

It makes me wonder if I’m going to end up feeling empty once I reach “the number.” When you finally grab ahold of that next level, the happiness squirms out of your hands and makes you chase it once again.

Ramit Sethi says to live a Rich Life now and an even Richer Life tomorrow.

A Rich Life is more than just some number on a spreadsheet (or checking my net worth on Personal Capital daily).

I like that. It seems to resolve my scarcity mindset and phobia of “running out” every time I go out.

  • But I’m already addicted to the chase—the constant upward trajectory and the mirage of security and self-worth tied to it.
  • I’m already addicted to logging my expenses on the Excel spreadsheet I started in 2008 and feeling clean when I see that it’s on track to stay under my $1,200 non-rent monthly budget.
  • I’m already addicted to forecasting the year’s income and the percentage spent on rent and investments.
  • I’m already addicted to projecting when I’ll reach financial independence or FIRE (at which point I’ll keep working anyway but not feel so anxious).

Just one more high score. Just one more hit.

At this point in the upward trajectory, does happiness lie above or below?







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