The Real Reason Career Decisions Feel So Hard

I spent three months deciding whether to leave my last job. Spreadsheets, conversations with mentors, sleepless nights. In the end, what finally made the decision clear had nothing to do with any of that.

I asked myself one question: "Which choice lets me be more of who I want to be?"

The job with better pay but longer hours? It conflicted with my actual priority at the time: being present for my family. Once I admitted that to myself, the decision made itself.

Why Career Decisions Trip Us Up

Most career advice focuses on external factors: salary, title, company prestige, growth potential. These matter. But they're not why decisions feel hard.

Decisions feel hard when you haven't admitted what you actually care about.

The person agonizing over two job offers often isn't confused about the jobs. They're confused about themselves. Do I value security or adventure? Am I willing to sacrifice income for flexibility? Is my ego driving this, or my actual interests?

A Different Approach

Before you make a spreadsheet, sit with this:

What do you want your average Tuesday to look like? Not the highlight reel. The boring, regular day. Do you want to be in an office or remote? In meetings or heads-down? Managing people or building things?

What have you regretted in past jobs? Not what went wrong externally, but what you wish you'd prioritized differently. Those regrets reveal your actual values.

If both options paid the same, which would you choose? This strips away a lot of noise.

The Trap of "Optimizing"

You can't optimize your way to the right career. Life isn't a spreadsheet. The job that looks perfect on paper might make you miserable. The "risky" move might be exactly what you need.

I've watched friends take prestigious roles they hated because they couldn't justify saying no. I've watched others turn down more money because they knew the extra stress wasn't worth it for them.

Neither choice was universally right. Each was right for that person at that time.

What Actually Helps

Get clear on 3-4 things that genuinely matter to you in work. Not what should matter. What actually does. Be honest, even if it's uncomfortable.

Then evaluate your options against those things. Not against what looks impressive or what others would choose.

The goal isn't to make the optimal decision. It's to make a decision you can stand behind because it reflects what you actually care about.

Everything else is noise.