You’re Not Behind. The Timeline Was Built for a Different Time.

Over the last couple of years of conversations with friends, peers, and generally those in their 30s & and 40s, I’ve noticed that a lot of people nowadays feel “behind” in life. Thinking about myself at 36, I recognize that I’ve accomplished a lot of things that the younger version of me would be proud of, like building a career I never thought I would have, moving to Los Angeles, buying a home, traveling the world, and being in a loving relationship with an amazing woman. If you had painted this picture to me at 25, I probably would have assumed that I had everything figured out.

Yet somehow, I can still feel behind.

There are still times when I look at peers with a bigger title, who make more than me, run successful businesses, have actually published a book, are married, own a nicer home, etc., and I immediately question whether I’ve done enough with my life up to this point. It doesn’t really matter what I have already accomplished because there is always another version of adulthood waiting to remind me that I am late. Social media obviously makes this worse because we are constantly seeing everybody else’s major announcements without seeing the anxiety, debt, arguments, loneliness, or uncertainty that may exist behind them. Still, I don’t think comparison is the only reason so many of us feel this way.

A lot of us are measuring ourselves against a timeline that was built for a different time.

There’s a typical set of standards, expectations, and milestones that we’ve all instilled in our brains growing up: finish school, get a good job, move your way up the company, get married, buy a home, have a family, and retire with enough money to enjoy the remainder of your life that you spent decades working for. While that may not be the exact order of events, the basic promise handed down to us by our parents (and society) was that if you work hard and make responsible decisions, your life should get easier and more stable as you get older. Unfortunately, that’s not really how life feels for a lot of us anymore.

As someone who wasn’t around during the older times, I’m not trying to claim that the previous generations had easy lives compared to ours. However, I do think the traditional version of adulthood assumed a level of predictability that made sense for a pre-internet (and pre-AI) era and doesn’t really fit a lot of the way the world functions nowadays. The old way of life assumed that a good job would always be available to those who worked hard and did enough, while their salary would also rise enough to keep up with living expenses, eventually resulting in a new car, a new home, and all the necessary funds to support a family.

Nowadays, you can excel at your job and still be laid off because the company changed direction, needed to reduce costs, or sometimes for no given reason at all. Salaries and wages are arguably higher than we ever dreamed of when we were kids, and it still isn’t enough to cover all of your basic living expenses on top of having anything left over to spend. It’s crazy to me that six figures used to be such an accomplishment, and nowadays, depending on where you live, it’s borderline poverty. A lot of us spend years building our careers, only to realize that the corporate ladder we’ve been climbing is constantly being moved, shortened, or just removed completely.

The problem with all of this? When we can’t follow the timeline as it was presented to us as kids, we assume that something must be wrong with us. You should have saved more. You shouldn’t have taken that job opportunity and stayed in your comfortable gig. You shouldn’t have done this. You should have done that. I mean, sometimes these questions to ourselves are fair, as we’ve all made bad decisions, wasted money, avoided uncomfortable decisions, and stayed in shitty situations longer than we should have, which we could have avoided by being a little more introspective. Not all of our life problems can be blamed on the economy or the current state of society, but I do think there’s an increasing number of us who are victims of an outdated rubric that we’re evaluating ourselves on.

Ultimately, we need to unlearn a lot of what we were taught growing up and find a different way to measure our progress in life.

Instead of only looking forward and wondering where you could have reached that next milestone, maybe we need to ask ourselves whether we are becoming more resilient to what life throws at us. Are we able to handle a difficult month better than we could have five years ago? Do we have a support group that we can rely on when something does go wrong? Are we building skills, savings, relationships, and experiences that make us stronger even if they don’t get publicly displayed on Instagram? Are we moving towards a life that we actually want, or are we chasing things because we’re afraid of how it looks if we don’t? While some of these questions may seem less exciting than chasing a promotion, planning a wedding, or buying a new house, they do tell us more about whether our lives are actually improving. Someone can look far ahead on social media while being deeply unhappy, financially overextended, or trapped in a life they never consciously chose. Someone else can look behind while rebuilding after a layoff, leaving the wrong relationship, changing careers, or finally learning how to take care of themselves.

I do also want to say that I’m not pretending that milestones don’t matter. For me, I still want to build an even better career, continue to unlock financial freedom, finish my book, and travel the world. The ambition and drive are still there, but they’re now sitting beside a version of me that’s also trying to recognize that as I get older, these milestones don’t determine whether I’ve lived properly.

All of us are responsible for deciding what we do next, but you’re also allowed to stop punishing yourself for not following a plan that was written for a world that no longer exists.