Feeling Stuck and Behind in Your 20s? Let’s Untangle What’s Really Going On

Let’s use the analogy of a car. If your car isn’t working but you don’t know what’s wrong with it, it can’t get fixed. The same goes for feelings. If we don’t know where this “behind” feeling is actually coming from, it’s going to be a lot harder to work through. Let’s pop the hood and see what’s really going on underneath the surface.

It’s very possible you’re measuring where you “should” be in life against your peers, influencers you follow, and the beliefs your parents instilled in you. When you “should” yourself, you’re creating rigid rules you feel you have to live by, and you automatically set yourself up to feel guilt and shame when you don’t measure up.

Tip #1: Replace “should,” “must,” and “ought” with “prefer” or “want.”

Instead of: “I should be married by now.” Try: “I want to be in a committed relationship.”

When you say you’d prefer to be at a certain place in life, you’re acknowledging your goals and dreams without turning them into demands. When you stop “shoulding” yourself and start acknowledging your preferences, you create more room to be gentle and kind with yourself, which actually makes it easier to take steps toward the change you want.

Food for thought: when you “should” yourself and compare yourself to where other people are, you’re spending more time focused on them than on you. Don’t you need to focus on yourself to move forward?

A lot of people know exactly what changes would help them feel better, but they still don’t make them. That can come from a few different places, and one of the biggest is avoidance. Even though you want change, not changing is comfortable. It’s familiar and it’s almost always easier to stay in your comfort zone than to try something new. I know it’s cliché, but how do you expect to grow if you never leave your comfort zone? Stepping into discomfort is scary, but scary isn’t the same as harmful.

You might also be feeling stuck due to a fear of failing or making the wrong decision. What if you stopped labeling decisions as “right” or “wrong” and instead acknowledged that there are simply two paths, each with its own pros and cons? Remember, waiting for the “perfect” choice is still a choice, and it’s the one that keeps you stuck.

Tip #2: Practice making decisions before you feel “ready.”

Waiting until you feel certain is a form of avoidance. Action creates clarity, not the other way around.

Lastly, you might feel worried about how other people are going to perceive you. If you make a career change or start dating someone new, you might wonder, will people judge me? Will they like my new partner? Will they think I’m making a mistake? There’s a chance some people will disagree with your choices, but if you act out of fear of what other people might think, you’re essentially letting them dictate how you live your life. Plus, you can’t actually read their minds. There’s a really good chance you’ll never even know what people think, and you’ll have given up something that mattered to you for a reaction that may not even exist. If close family, friends and coworkers do have opinions, therapy can help you sort through those feelings and figure out where their approval ends and your own values begin.

Tip #3: When you notice yourself avoiding something because of what people might think, ask yourself: what’s the cost of not doing it?

Your 20s are a pivotal decade, and honestly, that’s exactly why it’s so easy to feel lost in them. There’s a lot happening at once, so let’s get into some of it.

Your identity is still forming. Who you are at 21 can be completely different from who you are at 29. Maybe you’re still figuring out what you actually value, separate from what you were raised to value. Maybe your sense of self leans a little too heavily on work, productivity or a relationship. When one of those things shifts, your sense of self shifts with it. There’s no guidebook for how you’re “supposed” to live your life. It’s totally okay to feel lost.

Friendships are changing in ways you didn’t expect. You might be grieving the closeness you once had with a childhood friend, college roommate, or work bestie. The people who used to be daily texts and FaceTimes are now a “we should catch up soon” that never quite happens. Maybe setting boundaries with friends is much harder than you anticipated. So much is changing around you, and you might feel like you’re the one thing that isn’t moving at all.

Everyone seems to be on a different timeline. You might have single friends, engaged friends, married friends, and friends with babies. Since there’s no shared milestone schedule anymore, it’s quite difficult not to measure yourself against the people who seem to have “more.” Comparison is a very human, almost automatic response. The problem isn’t that you compare. It’s the conclusion you draw from it: that you’re the one who’s behind.

So, if your 20s feel disorienting and way more difficult than you ever imagined, it’s not because you’re doing them wrong. It’s because this decade is genuinely a lot,  and for the first time, no one’s handing you a map.

Feeling stuck doesn’t mean you’re failing. Remember, stuck is a feeling, and like any feeling, it shifts when you change what you’re telling yourself and what you’re doing (or avoiding). Maybe feeling stuck actually means you’re contemplating a decision you’re scared to get wrong, sitting in discomfort you’ve been taught to avoid, or holding yourself to a “should” that was never yours to begin with. Your 20s are full of uncertainty, and uncertainty has a way of creating a narrative full of self-doubt and worst-case scenarios.

You don’t have to have it all figured out. You just have to take one step, then another, without waiting to feel completely ready. Clarity comes from moving, not from standing still and thinking harder.

If you’re tired of feeling stuck and ready to start moving forward, even when the path isn’t clear, I’d love to help. I specialize in working with young adults navigating the ups and downs of life transitions. I offer a free 20-minute consultation call where we can talk about what’s keeping you stuck and how therapy can help. You can book yours here.