Have you ever caught yourself saying, “I should have achieved more by now”? “I should be married,” “I should have figured out my career,” or “I should be happier? Then you have found yourself in the timeline trap. A trap that has evolved over time making folks run like crazy to some preset time goals.
This thinking sabotage confidence, create anxiety, and drain joy from otherwise fulfilling lives. Let’s unpack this trap and explore how to reclaim your timeline—on your own terms.
The Timeline Trap is the belief that our lives must unfold according to a strong, preset schedule, often defined by culture, family, peers, or social media. This invisible checklist might look like: Graduate by 22, Dream job by 25, Married by 28, First child by 30, Successful career and happy family by 35, retire with lot of assets by 60 and live a slow retired life later. When we feel we haven’t reached this target, no matter how well we are doing we feel we have lost, we feel we haven’t done enough. This is the essence of the timeline trap.
Another dimension of this timeline trap is the very toxic phrase “should have”, you might wonder why I am calling it toxic, here’s why it subtly implies that you’re behind, inadequate, or broken. It makes you feel you have lost something; you haven’t reached your goal, you failed. It focuses on regret, fosters comparison, and removes you from the present moment. Worse, it ignores the truth: everyone’s journey is different. But is the “should have” attitude affecting us you might wonder, but this phrase can lead to
- Anxiety and shame: Constant comparison leads to feelings of not being enough.
- Decision paralysis: Fear of “falling behind” prevents people from making aligned choices.
- Missed opportunities: Chasing timelines can blind you to paths better suited to your values and strengths.
Where does this timeline trap originate from? Where are its roots? The roots of the Timeline Trap are often external, Cultural beliefs, every culture has a preset timeline for its people. This could just be based on an average performance of the community, but it makes a very string effect in pulling one into the timeline trap.
Social media: you open social media you see people posting graduations, weddings, pregnancies, promotions, new ventures but we never see failures, comebacks, downfalls, struggles or the pain. This wires us into thinking that the people on the media is doing much better than us. Sinking us into the I should have trap again.
Family and peers comparisons, my cousin started working when she was just 21 !, my aunt did this at 30, my friend is getting married at 25 and the list just goes on and on. This comparison and pressure within the family and friends can draw us into the timeline trap.
What we forget is that these expectations aren’t laws—they’re opinions.
How to escape this trap? Lets dive into that;
1. Identify Your ‘Shoulds’
Make a list of all the things you believe you should have achieved by now. Examine where each belief comes from. Is it from your own inner truth—or an external narrative?
2. Reframe the Narrative Replace “I should have” with “I’m choosing to.”
Example: “I should have a better job” → “I’m choosing to explore work that feels meaningful.”
3. Redefine Success for Yourself
What does success look like for you—not your friends, not your family, not your followers? Take time to define your own vision of a fulfilling life.
4. Practice Self-Compassion
Remind yourself that you’re not late or behind—you’re growing, learning, and evolving. Progress isn’t always linear.
5. Celebrate Non-Linear Growth
Learn to value the inner milestones—resilience, healing, courage, setting boundaries. These are often more transformative than job titles or wedding dates.
6. Tune Into Your Values
When you make choices from your values instead of a timeline, you reclaim your power. Live guided by what matters to you, not what looks good on paper.
7. Set Aligned Goals—Not Deadline-Driven Ones
It’s great to have goals, but let them be flexible and values-driven. Replace “I must do this by 30” with “I want to move toward this in a way that feels right for me.”
The idea that life has a universal timeline is a myth. Life isn’t a race. Everyone runs at their own pace.
One might reach the peak of career at 35 another at 22 or maybe even at 52. They key is to realize that you need to run at your pace, not at a preset pace.