When 'Should' Stops Working
There will never be a shortage of people who think you should be doing something differently - and no amount of agreement will make you feel safe. You’ll never find fulfillment through other people’s expectations either.
I spent 20 years as the ultimate people pleaser and this is the one true law I learned:
Doing what you ‘should’ do only works until you actually need to show up for yourself.
Those familiar with this have a difficult time changing because they don’t understand the cost of staying in it or the reward for getting out:
Exhaustion from overthinking. Trying to be the ideal version for everyone means overpreparing endlessly on behalf of others.
Zero self-confidence. Hesitating, second-guessing, and always letting others lead before me meant I never became the leader I thought I could be.
Lack of respect. I had little respect for myself and even when others thought me as a kind or considerate person, few people respected (or saw) the real me.
The flip toward self-honesty and authenticity wasn’t instant. I had to work at it.
If it took 20+ years to build, I promise it won’t change in a day. As ‘tough-writing’ as this may be sound, the process for me was incredibly painful. There were countless days spent mourning the person I was and the person I had not yet become.
But the moments I was myself - without fear of judgement - were intoxicating:
Conversations felt richer in the moments I spoke freely instead of saying what I thought the other person wanted to hear, leading to more laughter and deeper connection.
Everyday choices gained meaning when I chose what resonated with me, rather than what I was ‘supposed’ to value.
Goals became deliberate decisions. They were no longer just tasks to achieve, but journeys I could savor.
The day I let myself be fully honest, I felt a genuine love for myself that I hadn’t realized was possible.
Today, the ‘shoulds’ still appear. But I notice them, and they no longer dictate my choices. They are no longer my duty to fulfill.
The self-respect I gained by letting go is more meaningful than I could imagined back then. It only gets better from here.