Devon Chichester

May 27, 2026

Our twenties are often chronicled in the media as the most lively, opportunistic chapter of our lives. During this era of life one occupies a unique middle-ground, being perceived simultaneously as an adult who is contributing to society and a youth who is entitled to some immature fun. The idea of such boundless opportunity, however, can feel overwhelming; A looming reminder one is never doing quite enough to make use of it. 

Focus on building your career. Achieve success and stability as young as possible. But, be careful not to isolate yourself—you’re still young! Meet the love of your life! Go out! But don’t go out too much, or you risk being perceived as immature, unfocused. 

How does one manage to uphold these two opposite ends of the spectrum?

As a 24 year old post-graduate living in Boston, I’m still figuring that out. As a student, I thrived within the structure school provided and considered myself a competitive candidate for success. Now, two years after graduating, I’m still working as a restaurant server—the job I took up the summer after graduation, intent on finding something in my field by the fall.

 I often grapple with whether I should abandon the aspirations I’ve carried throughout most of my life. The job market stands in a difficult place for everyone. Personally, I often find myself feeling washed up, having failed to do as much as possible as early as possible to jumpstart my career. Have I become obsolete to recruiters at just 24 years old? 

The open positions that I’ve encountered tend to require one of two things: several years of professional experience, or current enrollment in college or graduate school. I know I have the abilities and the ambition to succeed in the roles I apply to. But, in an awkward stage where I’m not experienced enough to be a seasoned professional yet I’m past the point of being seen as a ball of clay waiting to be molded, I find myself always coming up short. 

Still, when I reflect on the things I’ve done and the choices I’ve made since college, I can’t quite regret any of them. Maybe if I had pursued another internship or got an earlier start on joining campus organizations, I would have secured a position right out of graduation and climbed the ladder from there. But I can’t help but think I also would have grown less as a person. 

I started working as a server straight out of graduation so that I could save up some money while looking for a full time job. I had never worked in a restaurant before, the closest experience being a semester-long stint at a campus coffee shop. I had always been relatively social, but my measure of sociability was based almost entirely on school experiences: twelve years in my hometown and four at college, which had started at an admittedly anti-social time in everybody’s life, the height of the covid pandemic. 

Working as a server, I was pushed far out of that bubble. Both my coworkers and the customers I encounter come from an unimaginably wide range of backgrounds with an unimaginable breadth of stories to tell. I was humbled by the fact that what I had seen as a temporary stepping stone was, for many others, a career that supported entire families. I developed a thicker skin through serving people of all different temperaments, keeping my cool during interactions that I probably would have cried at two years prior. Most importantly, I’ve gained a stronger sense of self and perspective that I didn’t even realize I lacked before. 

If you’d told my high school self that, two years after graduating I was still waiting tables and hadn’t found a footing in my career, I would wonder where I fell off course. If you had also told me that I’d manage to move out into my own apartment while paying off my loans, traveling, and carving out my own little part of the city I’ve always lived just outside of, maybe I’d give myself some grace. 

How do you survive your 20’s in 2026? I’ll let you know once I do. For now, my advice is this: Just live them. Wherever you are, it’s probably where you’re supposed to be. Don’t rush so relentlessly to the next rung of the ladder that you fail to extract all the value from the one you’re on now.