The Worst Part About Jobs in Your 20’s

The most important realization I’ve had about jobs-in-your-20s is simply this: You’re perpetually at the bottom. I can’t tell you how many times I’ve heard the whole “can’t-get-a-job-without-experience / can’t-get-experience-without-a-job” paradox. It makes sense. You don’t have any experience yet, and the way most economic structures are set up, there’s little to no way in hell you can skip any rungs of the ladder.

1. No one is “killing it”…

The reality of working in your twenties is that almost nobody has it figured out. People you meet seem to have a plan, a title, and momentum — and you are somewhere near the bottom rung, still figuring out which direction the ladder even goes. The gap between how it looks from the outside and how it actually feels is the part nobody posts about.

2. …But Everyone Makes it Look Like They Are

Social media makes the highlight reel look like the whole story. What you compare against is other people’s edited versions of their first decade of work — not the decade itself. If your comparison set is a curated feed, you will always conclude that you are behind.

3. Jobs are mostly a decade-long speed dating game.

Your first job is rarely your last. A lot of early career life is a series of short relationships with roles, companies and industries, each one teaching you something about what you actually want. Along the way, an entry-level position may be only marginally related to the degree you studied — relevance to your field of study is often thin, and the learning happens sideways.

Read more about job searching in your 20s, 30s and beyond at The Ladders.

Call to Action

If any of this sounds familiar, you are not alone — and the good news is that the way out is usually a better process, not a lucky break. Grab the short checklist below for the steps that worked for me.